7 Underrated Missouri Towns Worth the Drive in 2026
Underrated destinations often prove to be the best places to visit. Low expectations lead to pleasant surprises, and fewer crowds make it easy to explore at your own pace. Missouri has much to offer the traveler who prefers less popular spots, where you can stroll along a frontier-style boardwalk in Arrow Rock, bike America’s longest rail-trail in Rocheport, taste wine, spirits, and craft beer galore in Hermann and Ste. Geneviève, or discover an authentic 1600s London church in Fulton. Here are seven underrated Missouri towns worth the drive in 2026.
Rocheport
Many have stumbled upon Rocheport while hiking or biking America’s longest developed rail-trail at Katy Trail State Park. The 240-mile-long former corridor of the Missouri-Kansas-Texas Railroad is a designated Millennium Legacy Trail, part of the American Discovery Trail, and also a Rails-to-Trails Conservancy Hall of Famer that meanders along the scenic Missouri. Cyclists would argue Merriweather Café & Bike Shop serves the best breakfast this side of the Missouri. This popular spot along the Katy Trail offers a warm welcome, an expansive patio, and yummy breakfasts made to order of both the savory and sweet variety.
However, Rocheport is a pleasant drive from Kansas City, where its peaceful location along the Missouri River feels untouched by the stress of modern-day life. Recently celebrating its 200th birthday, the town has far more to offer visitors than oodles of historic charm and bike trails. Wine enthusiasts discover award-winning varietals at The Blufftop at Rocheport, where tastings and flights by Les Bourgeois Vineyards are available. The original site of the winery is now The A-Frame Winegarden, overlooking the river in an idyllic spot to sip wine and share dishes from the picnic-style menu. An eclectic mix of original fine art, antiques, and estate finds is also scattered through town, including Art & Antiques and Blacksmith Shop. Open on weekends at the pre-Civil War Hill House, the site also includes The Red Dog Forge, where the blacksmith expresses his creativity through customized work.
Hermann
Hermann’s riverside location in Missouri Wine Country tends to see more visitors during its many festivals. However, German and American ingenuity created a town worth exploring year-round with a selection of spirits, wine, and beer. It is best to assign a designated driver for this 90-minute drive from St. Louis, as a tippler’s tour around town includes two breweries, six wineries, and four distilleries. The Fernweh Distillery’s craft cocktail bar, located in an 1867 historic building, offers samples of small-batch and single-barrel spirits distilled next door, paired with a menu of hearty American and German-influenced fare.
Experience a taste of Missouri’s winemaking history at the Reserve Cellars of Hermann, where the press house and cellar were used by George Husmann, Missouri’s father of viticulture. The historic Hermann Farm + Museum property is a beautiful setting to sample blends from the winery's Missouri and California vineyards, and you can discover your inner craft beer enthusiast sampling authentic German-style brews in a century-old tin mill at the Tin Mill Brewing Company. Imported barley, hops, and copper brewing kettles from the Hallertau region of Germany ensure the brewery adheres to the German Purity Law of 1516 as they experiment with its version of pilsners, lagers, and IPAs. Authentic “Isar” Tankards from Munich, Bavarian pretzels, and locally made bratwurst on a bun complete your Lieblingslokal experience, where guests are always sure to find a place at the table.
Parkville
As part of the Kansas City metropolitan area, Parkville might get overlooked as nothing more than a “suburb.” However, it has much to offer road trippers looking for a day of foodie or “spirited” fun. Nearby Parkville satisfies curious palates and upscale foodie adventurers in one lovely spot where you can indulge your senses in a romantic setting or settle in at less intimate establishments. Café des Amis is a quaint second-floor eatery that transports you to a Paris bistro with charming views of the town’s main street treetops while dining on romantic French dishes paired with a selection of fine wines. Newcomer Parkville Wine House is your destination to join fellow imbibers at family-style tables, sampling delectable wines, craft beers, and spirits paired with a mix of quality charcuterie boards or artisanal sandwiches in a beautifully restored 100-year-old house.
The premium American Wagyu beef collection at KC Cattle Company shows you that Japan is not the only country producing mouthwatering beef. If you tend to sniff your nose at the humble hot dog, you will soon discover there is nothing humble about the legendary Wagyu hot dogs at KC once they hit your grill back home. You can also shop and taste your way through Parkville Trading Post, a nostalgic spot to explore a collection of antiques and gifts along with sweet temptations, including retro candies, hand-dipped ice cream, and homemade fudge and chocolates. Sublime.
Arrow Rock
Arrow Rock's Main Street boardwalk captures the town’s early 1900s vibe, where some of America's best-kept history secrets are hidden in gift shops, lodges, and a historic gunsmith shop. History buffs will find plenty of intrigue and surprises beyond that dusty boardwalk they might have otherwise overlooked. Firearms enthusiasts will not want to miss Arrow Rock 1829 Gift Shop's impressive Christopher Collection of Early Missouri Firearms and gunsmithing demonstrations at The John P. Sites Jr. Gunsmith Shop. As America’s last known restored gunsmith shop still at its original location, this site offers insights into the methods used by the shop's original owner, a 23-year-old gunsmith whose exceptional rifle work made him one of America’s most respected artisans.
Brown Lodge No. 22 is Arrow Rock’s first black lodge, the town’s one remaining hall of the Ancient Free and Accepted Masons, and one of many lodges resulting from the first all-black Masonic Lodge. Established by free black man Prince Hall in the mid-1780s, all-black lodges provided social and financial support in the pre-insurance and pre-social welfare era, making Arrow Rock’s Black History Museum an interesting chapter of black heritage worth exploring. The town is also home to pioneering doctor John Sappington, one of the first doctors to treat fevers and malaria with quinine. The Dr. John Sappington Memorial Museum honors his groundbreaking work and advanced treatments using "Dr. Sappington’s Anti-Fever Pills."
Ste. Geneviève
Despite being Missouri’s oldest permanent European settlement, Ste. Geneviève is sometimes overlooked by American history buffs who might feel it has stronger ties to French Canadian heritage than the American Revolution. Just an hour from St. Louis, this Mississippi River town offers authentic French-colonial architecture along narrow streets with old-world aesthetics and gave way to a thriving art colony in the early 1930s. Depression-era-themed art that explored the human condition produced significant American Regionalism works by Thomas Hart Benton and socially conscious works by Joe Jones. The collections at Sainte Genevieve Art Center & Museum speak to the town’s influences on emerging artists of the time.
Historic structures at the Ste. Geneviève National Historical Park demonstrates unique building methods and architecture, including the town’s oldest standing building, Green Tree Tavern. Tour the simple home of a formerly enslaved woman married to a Frenchman and the more stately home of the Commandant who oversaw the town’s transition following the Louisiana Purchase. The limestone hills surrounding Ste. Geneviève are dotted with historic stone farmhouses along one of America’s most unique wine routes, Route du Vin. Charleville Brewery & Winery is a well-rounded destination with a tasting room featuring 24 self-serve beers, wines, and “Charle-rita” taps, upscale casual fare made for sharing, breathtaking views, warming fire pits, and a restored 1860s log cabin for overnight stays.
Fulton
Fulton tends to fall under the radar with tourists who underestimate its attractions. However, there are plenty of reasons Fulton is known as the “Kingdom of Callaway.” Admirers of one of Britain’s most prominent WWII figures, Winston Churchill, can visit America's National Churchill Museum at Westminster College to explore over 10,000 objects, including personal correspondence, original paintings, and various “Churchilliana.” The grounds are also home to a 1677 Christopher Wren-designed church, moved stone by stone, from London as a memorial honoring Churchill’s iconic “The Sinews of Peace” address. St. Mary the Virgin Aldermanbury's exterior was completed in May 1966, and the interiors were opened in 1969 to much fanfare by both British and American dignitaries. Campus ties to the Churchills continue at the Breakthrough sculpture, introduced a year after the fall of the Berlin Wall. The work by Churchill's granddaughter Edwina Sandys stands 11 feet high and 32 feet long and is often regarded as one of America’s most important monuments since the Vietnam War Memorial in 1982.
The Brick District is a character-filled area off-campus with red brick streets, wrought-iron lamp posts, 19th-century buildings, a quaint covered bridge, and charming eateries like the Post Office Bar & Grill, where you can treat yourself to drinks or a meal in a former post office.
Hannibal
Hannibal is a popular spot for bookworms with a passion for the work of Samuel Langhorne Clemens, aka Mark Twain. However, non-fans might avoid the town, worried it is overly “Twain.” Although Twain-centric, the riverboats, caves, and certain characters in his books create Hannibal-specific experiences worth the drive from St. Louis and further afield. Twain’s stories reflected the times, including the struggle of the enslaved people following the Civil War. Jim’s Journey: The Huck Finn Freedom Center is a unique museum that tells the story of Daniel Quarles, an enslaved person owned by Twain’s uncle, who lived in Hannibal after his emancipation. Over 600 artifacts tell the story of Quarles and his descendants through documents, photos, art, and memorabilia.
The Mark Twain Cave Complex takes you on an otherworldly journey through the Mark Twain and Cameron caves. Gunslinger enthusiasts will appreciate Twain’s cave, where the notorious Jesse James holed up after a robbery gone wrong in 1879. You can also tour Cameron Cave, exploring the maze of paths and strange rock formations by flashlight. Discover the magic of the Mississippi River aboard the Mark Twain Riverboat, taking in the sights on a lazy afternoon cruise or for a night of dining and dancing. Wander historic downtown Hannibal, admiring the colorful murals, and pop into the quirky Becky's Old Fashioned Ice Cream Parlor & Emporium for a treat and a distinctly Hannibal shopping experience.
This little road trip across the Show Me State is proof that these seven underrated Missouri towns are well worth the drive in 2026. When you ignore the obvious and focus on the intriguing, you are sure to discover less-traveled spots worth exploring, whether it is lunch at a French bistro in Parkville, a tribute to the resilience of enslaved Americans in Hannibal, or unraveling French-Canadian history in Ste. Geneviève. Hop in the car, and you can visit these delightful towns in less than two hours from urban centers like St. Louis or Kansas City.
